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Updated: Jul 11, 2025
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
6,7-Diphenyl-5-thia-7-aza-spiro-[2.6]nonan-8-one 5,5-dioxide
Hemant P Yennawar1, Michael W Russell2, Lee J Silverberg2
1Department of Biochemistry and Molecular Biology Pennsylvania State University, University Park, PA 16802, USA.
Abstract:
The racemic mixture of the title compound, C19H19NO3S, crystallizes in space group P with two homochiral mol-ecules in each asymmetric unit. The seven-membered ring in both mol-ecules is in a pucker-chair conformation. The extended structure exhibits C-H⋯O hydrogen bonds, of which two connect crystallographically independent mol-ecules to generate a chain propagating along the b-axis direction. One C-H grouping of the cyclo-propyl ring is in close contact with the phenyl ring of the neighboring independent mol-ecule in C-H⋯π type inter-actions with carbon atom-ring-centroid distances of 3.544 (5) and 3.596 (4) Å. Other inter-actions are of the parallel-reciprocal type, with the chiral carbon atom of one mol-ecule donating a proton to an oxygen atom of the sulfone group of a symmetry-related mol-ecule and vice-versa. Symmetry-related mol-ecular pairs also exhibit T-type inter-actions between aromatic rings with inter-planar angles of 74.2 (2) and 69.2 (2)° and inter-centroid distances of 4.965 (4) and 5.114 (4) Å.
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